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Full text of "Practical Organic Chemistry"

JLYLCYANIDE

effected by running the water very slowly through the condenser
so that the upper part remains warm. Theiodotoluene solidifies
in the receiver. It has a yellow tint, which may be removed by
recrystallisation from spirit. Yield, 45—50 grams.

NaHSO4+HoO.
CH3.C(5H1N,,SO,H + KI = CH,.C«H4I + N2+ KHSO4.
Properties.—-Colourless plates ; m. p. 35° ; b. p. 211—212°.
1.  Tolyliodochloride.—Dissolve TO grams iodotoluene in
five times its weight of chloroform, cool in ice, and pass in dry
chlorine until saturated.    If a chlorine cylinder is not available,
the chlorine  is  conveniently made by dropping concentrated
hydrochloric acid from a tap-funnel on to powdered potassium
bichromate or permanganate in a round flask, heated on the
water-bath.    The    chlorine    is    dried   through    concentrated
sulphuric   acid.    When   chlorine   is   no   longer absorbed, the
yellow needle-shaped crystals of the ioclochloride are filtered,
washed with a little chloroform, and dried on a porous plate.
CH3.C0H4I + C13= CH3.CaH4ICl2.
2.  lodosotoluene.—Dissolve 2-5 grams caustic soda in 20
c.c. water, and grind with 5 grams of iodochloricle in a mortar.
Leave  overnight and  then  filter and wash with water.    The
colourless crystals of the iodoso-compound are dried on a porous
plate.
CIl;,C(;H.llCl.H-2Na()H = CH;t.CtiHJO + 2NaCl + H2O.
See Appendix, p. 285.
PRKPARATION 68.
/CM,    i
p-Tolylcyanide, C,.!!,^
X:N   4
Sandmeyer, />Vr., 1884, 17, 2653.
20 grins, /-toluidine.
45 c.c. cone, hydrochloric acid (in 150 c.c. water).
16 grins, sodium nitrite (in 40 c.c. water).
50    „    copper sulphate (in 200 c.c. water).
55     „    potassium cyanide (in 100 c.c. water).
The copper sulphate is dissolved  in 200. c.c. water on the
water-bath in a round flask (2 litres).    Pure potassium cyanide